NP-MRD: Showing NP-Card for pyriculol (NP0191451)

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Record Information

Version

1.0

Created at

2022-09-04 08:25:28 UTC

Updated at

2022-09-04 08:25:28 UTC

NP-MRD ID

NP0191451

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pyriculol

Description

Pyriculol belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. Pyriculol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. pyriculol is found in Pyricularia grisea. It was first documented in 2022 (PMID: 36068077). Based on a literature review a significant number of articles have been published on pyriculol (PMID: 36068076) (PMID: 36068075) (PMID: 36068074) (PMID: 36068073).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.8016    1.9024   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0705    0.7122    0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2527   -0.0187   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5686   -1.1657    0.3186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3810   -1.9707    1.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3354   -0.8496    1.1234 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5954   -0.1808    2.2984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104   -0.1313    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9946   -0.4122    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0183    0.2329   -0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415    1.2131   -1.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7494    1.8059   -2.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0638    1.4698   -1.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3833    0.4770   -0.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7114    0.1903   -0.8354 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635   -0.1232   -0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7157   -1.1511    0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8737   -1.5363    0.9748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8294    1.6073   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9838    2.5897    0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2344    2.4356   -0.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2071    0.4246    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1095    0.2620   -1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2186   -1.8492   -0.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1546   -1.8889    2.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -1.8347    1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    0.7848    2.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160    0.6187   -0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933   -1.1804    1.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285    1.5233   -1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4778    2.5743   -2.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8636    1.9389   -2.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1472   -0.4475   -0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9254   -1.6438    1.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  6
  5 25  1  0
  6 26  1  1
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 17 34  1  0
M  END


  Mrv1652309042210252D          

 18 18  0  0  1  0            999 V2000
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0191451

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\[C@H](O)[C@H](O)\C=C\C1=CC=CC(O)=C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O4/c1-2-4-13(17)14(18)8-7-10-5-3-6-12(16)11(10)9-15/h2-9,13-14,16-18H,1H3/b4-2+,8-7+/t13-,14+/m0/s1

> <INCHI_KEY>
YUQDGJSYYKKISE-COOXUBAGSA-N

> <FORMULA>
C14H16O4

> <MOLECULAR_WEIGHT>
248.278

> <EXACT_MASS>
248.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.965127554845772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1E,3R,4S,5E)-3,4-dihydroxyhepta-1,5-dien-1-yl]-6-hydroxybenzaldehyde

> <JCHEM_LOGP>
2.422065691

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.473035559879229

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.345957297111521

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3295326790183104

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
72.22630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1E,3R,4S,5E)-3,4-dihydroxyhepta-1,5-dien-1-yl]-6-hydroxybenzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
2-((1E,5E)-(3R,4S)-3,4-Dihydroxy-hepta-1,5-dienyl)-6-hydroxy-benzaldehyde	ChEBI
2-[(1E,3R,4S,5E)-3,4-Dihydroxy-1,5-heptadienyl]-6-hydroxybenzaldehyde	ChEBI

Chemical Formula

C₁₄H₁₆O₄

Average Mass

248.2780 Da

Monoisotopic Mass

248.10486 Da

IUPAC Name

2-[(1E,3R,4S,5E)-3,4-dihydroxyhepta-1,5-dien-1-yl]-6-hydroxybenzaldehyde

Traditional Name

2-[(1E,3R,4S,5E)-3,4-dihydroxyhepta-1,5-dien-1-yl]-6-hydroxybenzaldehyde

CAS Registry Number

Not Available

SMILES

C\C=C\[C@H](O)[C@H](O)\C=C\C1=CC=CC(O)=C1C=O

InChI Identifier

InChI=1S/C14H16O4/c1-2-4-13(17)14(18)8-7-10-5-3-6-12(16)11(10)9-15/h2-9,13-14,16-18H,1H3/b4-2+,8-7+/t13-,14+/m0/s1

InChI Key

YUQDGJSYYKKISE-COOXUBAGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Magnaporthe grisea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamyl alcohols

Sub Class

Not Available

Direct Parent

Cinnamyl alcohols

Alternative Parents

Substituents

Cinnamyl alcohol
Hydroxybenzaldehyde
Benzaldehyde
Benzoyl
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl-aldehyde
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
1,2-diol
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylpropanoid (CHEBI:80728 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.42	ChemAxon
pKa (Strongest Acidic)	8.35	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.23 m³·mol⁻¹	ChemAxon
Polarizability	25.97 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30791745

KEGG Compound ID

C16788

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13873378

PDB ID

Not Available

ChEBI ID

80728

Good Scents ID

Not Available

References

General References

Kazawa K, Kubo T, Akishita M, Ishii S: Long-term impact of the COVID-19 pandemic on facility- and home-dwelling people with dementia: Perspectives from professionals involved in dementia care. Geriatr Gerontol Int. 2022 Sep 6. doi: 10.1111/ggi.14465. [PubMed:36068077 ]
Arthur JD, Alamaw ED, Jampachairsri K, Sharp P, Nagamine CM, Huss MK, Pacharinsak C: Efficacy of 3 Buprenorphine Formulations for the Attenuation of Hypersensitivity after Plantar Incision in Immunodeficient NSG Mice. J Am Assoc Lab Anim Sci. 2022 Sep 6. doi: 10.30802/AALAS-JAALAS-22-000058. [PubMed:36068076 ]
Zhu N, Liu J, Ma T, Zhang Y, Lin Y: Fully digital versus conventional workflow for horizontal ridge augmentation with intraoral block bone: A randomized controlled clinical trial. Clin Implant Dent Relat Res. 2022 Sep 6. doi: 10.1111/cid.13129. [PubMed:36068075 ]
Gerstle EE, O'Connor K, Keenan KG, Slavens BA, Cobb SC: The Effect of Age and Fall History on Lower Extremity Neuromuscular Function During Descent of a Single Transition Step. J Aging Phys Act. 2022 Sep 5:1-8. doi: 10.1123/japa.2021-0521. [PubMed:36068074 ]
Chipperfield SR, Bissell P: "I Hear the Music and My Spirits Lift!" Pleasure and Ballroom Dancing for Community-Dwelling Older Adults. J Aging Phys Act. 2022 Sep 5:1-13. doi: 10.1123/japa.2021-0332. [PubMed:36068073 ]
LOTUS database [Link]

Showing NP-Card for pyriculol (NP0191451)

MOL for NP0191451 (pyriculol)

3D MOL for NP0191451 (pyriculol)

3D SDF for NP0191451 (pyriculol)

3D-SDF for NP0191451 (pyriculol)

PDB for NP0191451 (pyriculol)

3D PDB for NP0191451 (pyriculol)

SMILES for NP0191451 (pyriculol)

INCHI for NP0191451 (pyriculol)

Structure for NP0191451 (pyriculol)

3D Structure for NP0191451 (pyriculol)